5 Windward Ln, Madison, CT 06443
Property image
Property image
OFF MARKET

$1,721,200

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 3,214 sqft (on 0.52 acres)

5 Windward Ln, Madison, CT 06443

Madison Center
Est. Refi. Payment $11,888/mo*
Refinance Your Home
Currently Off Market - Sold Aug 23, 2019 for $1,012,000

Home Value

Trulia Estimate
$1.72M
Since last month
Decreased$7K (-0.4%)
Since last year
Increased$88K (+5.4%)
Since last sale
Increased$710K (+70.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +99% in the last 10 years
MonthEstimated value
2026
August 2026$1.72M
July 2026$1.73M
June 2026$1.76M
May 2026$1.71M
April 2026$1.68M
March 2026$1.65M
February 2026$1.61M
January 2026$1.62M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
513 Boston Post Road, Madison, CT
0.40
Single-Family Home
$1,100,000
12/18/25
4
2.5
3,031
55 Island Avenue, Madison, CT
0.22
Single-Family Home
$1,400,000
07/17/26
4
3
3,046
39 Madison Avenue, Madison, CT
0.36
Single-Family Home
$1,045,000
09/26/25
4
3
1,891
519 Boston Post Road, Madison, CT
0.39
Single-Family Home
$895,000
02/02/26
4
2.5
2,691
20 Cherry Lane, Madison, CT
0.36
Single-Family Home
$1,453,000
08/29/25
5
3.5
2,647
49 Middle Beach Rd, Madison, CT
0.31
Single-Family Home
$750,000
05/12/26
6
3
2,929
24 Cherry Lane, Madison, CT
0.35
Single-Family Home
$1,186,900
05/08/26
3
2.5
1,712
86B East Wharf Road, Madison, CT
0.47
Single-Family Home
$2,505,000
10/27/25
4
3.5
3,160
81A Middle Beach Road, Madison, CT
0.39
Single-Family Home
$2,495,000
08/17/26
4
2.5
3,321
11 Tuxis Road, Madison, CT
0.22
Single-Family Home
$1,175,000
03/25/26
4
2
1,692

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
3 Sunset Road, Madison, CT 06443
0.05
$1,272,100
3
2.5
1,980
Off Market
79 Island Avenue, Madison, CT 06443
0.06
$2,247,100
4
3.5
3,741
Off Market
10 Middle Beach Road West, Madison, CT 06443
0.05
$3,775,000
6
6
6,074
Recently Sold
15 Windward Lane, Madison, CT 06443
0.06
$1,682,700
4
3.5
2,704
Off Market
24 Windward Lane, Madison, CT 06443
0.06
$1,763,900
3
3.5
3,628
Off Market
11 Sunset Road, Madison, CT 06443
0.08
$1,324,300
3
3
2,186
Off Market
85 Island Avenue, Madison, CT 06443
0.09
$2,329,100
5
4.5
4,472
Off Market
14 Middle Beach Road West, Madison, CT 06443
0.09
$4,499,000
6
6.5
5,817
For Sale
34 Windward Lane, Madison, CT 06443
0.10
$1,921,400
3
2.5
2,756
Off Market
57 Island Avenue, Madison, CT 06443
0.15
$1,667,700
4
3.5
3,006
Off Market
4 Cambridge Drive #4, Madison, CT 06443
0.20
$1,062,200
2
2.5
2,358
Off Market
55 Island Avenue, Madison, CT 06443
0.22
$1,400,000
4
3
3,046
Recently Sold

Local Information

  • Map ViewExplore the area around 5 Windward Ln.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1973
Lot Size
0.52 acres
Living Area
3,214 sqft
Price/Sqft
$536
Parking
Garage

About this House

At the heart of seaside living, it is the relationship between the home and the water; this impeccable residence affords a lifestyle, an ease of living that will be enjoyed and coveted by the one lucky enough to live there. Perfectly sited on Windward Lane, this home boasts deeded beach that provides access to a "toes in the sand" beach and is also just a stone's throw to Madison's quaint village. The home lends itself to carefree living - exterior Hardie Board siding, each room impeccable, presented together by a functional and appealing floor plan. Gracious living room with fireplace, built-ins and book shelves opens to the dining room, a wonderful size for entertaining. The kitchen, which is truly the hub of the home, is outfitted with white cabinetry and granite counter tops with large, functional center island. Found in the rear of the home is a charming four season sun room- light and bright and a perfect place to relax with a good book. Desirable master bedroom with spa-like full bath is on the main level of the home. Cozy family room with fireplace, handsome office, laundry room and half bath complete the first level. The upstairs offers three more bedrooms, a nursery area as well as two more full baths. Enjoy the warmth of summer days sitting by brick patio or meandering on the lush lawn of the half acre parcel of professionally landscaped grounds. Truly an exceptional home in a wonderful beach community just waiting for the discriminating buyer.
5 Windward Ln, Madison, CT 06443 is a 4 bedroom, 4 bathroom, 3,214 sqft single-family home in Madison Center, built in 1973. It last sold for $1,012,000 on Aug 23, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,721,200, with a rent estimate of $5,672/month.

Home Details for 5 Windward Ln

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
Number of Rooms: 9Ceiling Fan
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: OtherGardenPatio
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1973
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 0.52 acres

Price and Tax history

DateEventPrice
Aug 23, 2019
Source: Smart MLS #170193894
Sold
$1,012,000
Jun 2, 2019
Source: Agent Provided
Pending
$1,100,000
May 13, 2019
Source: Agent Provided
Listed For Sale
$1,100,000
Sep 2, 1998
Source: N/A
Sold
$420,000

Market trends in Madison

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$710K
$53.67KMoM
Sale-to-List Price
101.6%
0.9%MoM
Price per sq ft
$334
$7MoM
Available listings
63
8MoM

Around this home

Neighborhood Overview

Madison Center
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Madison Center

At least 1 Trulia users voted on each feature.

  • 100 % Say it's walkable to grocery stores

  • 100 % Say it's walkable to restaurants

  • 100 % Say it's dog friendly

  • 100 % Say there's wildlife

  • 100 % Say neighbors are friendly

  • 50 % Say there are community events

  • 50 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Nancy Bussiere
    "My commute to work is under 15mins. I love the easy access to highways. There is public transportation available but I haven’t used it as of yet"
    0
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Frequently asked questions about 5 Windward Ln

  • What is 5 Windward Ln estimated to be worth?
    Trulia's estimated value for 5 Windward Ln in Madison, CT is $1,721,200.
  • What is the price history for 5 Windward Ln?
    5 Windward Ln in Madison, CT last sold for $1,012,000 in August 2019.
  • Is Madison a buyer's or seller's market?
    Madison is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Madison?
    The median sale price in Madison is $710K. That is down $53.67K from the prior month.
  • Does 5 Windward Ln have air conditioning?
    Yes, 5 Windward Ln in Madison, CT has air conditioning.
  • Does 5 Windward Ln have laundry facilities?
    Yes, 5 Windward Ln in Madison, CT has in-unit laundry.

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